Dana-boy Ch. 05

Brother Reg

Chapter 5

(Author's note: This chapter DOES contain scenes of GAY SEX and INCEST... You have been WARNED!)

My Mother the Fag-Hag...

It had been a few weeks since we had arrived here in Paradise and as I settled into my new gay-life style with Lord Sterling, even coming out and telling everyone that I was gay while he fucked me for the very first time... However, and now that the days were slipping past, I was also keeping an eye on the calendar, counting with anticipation the days and hours until my Mom would arrive to begin her extended stay during the per-Christmas run-up...

***

"Your Mother will be here in a few hours, would you like to meet her water taxi when it comes in?" Lord Sterling asked as we lay in his big bed, it was still early, 8am or so after waking to feel him nudging his big hard cock at my back entrance while spooning me under the sheets..

Sighing I could feel him grinding into me, his erect 9-inch cock was unmissable as I turned my face towards my pillow and offering a sleepy sounding "Uh-huh" in agreement but really what I wanted and what Lord Sterling could feel was me backing up into him, loving that feeling of stretching when first waking up and being hard in my cage, the yearning making me want my Lord's hard cock all the more...

"Oh so you like sex in the morning, Hmm? Yes, so do I... Roll over for me, lift your leg up, bend your one knee, that's it... Oh yess that's good... I love to fuck with a piss hard-on when I first wake up, it's so much more intense... Mmm... Can you feel me Dana-boy? Are you going to let your Lord and Master in?"

Uhhh... Oh yessss S-Sir... Lord Sterling... Your cock feels sooo good like this but... Uhhh! Oh! Aren't you going use any... Uhhh You know?... L-Lube?" I asked grunting some now as I felt him there, his cock head the size of a small apple and no longer resting but now he was pushing and moving forward, increasing the pressure, Lord Sterling was forcing his way in, splitting my tightened-up little pucker and attempting to fuck me dry...

"No Dana-boy not this time... I want you to feel me... All of me and with no assistance to help you... Remember your suffering and this is one of those times... Now, let's move, take your position, head down and ass up the way I like you... I'm going to fuck you and take you naturally...and yes, I know it will hurt...but that's the point"

Quivering now with my eyes growing wide I was suddenly cloaked in a sheen of cold sweat and feeling paralyzed as he stayed in behind me, his hands on my hips, helping to lift me into position. Scared now I knew that Lord Sterling fucking me 'naturally' or more like 'bone-dry' this wasn't going to be good... But worse of all, his causing me pain? it wasn't a deterrent but rather that's what was spurring him on... Making this hurt as I continued my suffering in his name...

"Uhhh! Oh nooo! Please my Lord nooo it.... Oh fuck it huu-uurts!" I cried then yelped as he gave me no rest period or time to think, let alone decide... Saying he owns me and proving it so, I felt my entire body go rigid. Resisting I was fighting him back the only way I knew how, I clenched my muscles tight all over including my ass!

My pink little back-door, I did what I could to keep it slammed shut, denying his entry as he pushed on, not giving up from his end either...

"Let me in Dana-boy... There is no sense in denying me what is mine... Remember, I own you now so relax yourself and let me in or I will drag you into the centre of town, naked as you and I'll fuck you while tied to the gates of the central square before I leave you there, ready for whoever wants you next... That choice is yours Dana... Where I fuck you... Not how or when.... Now do as your told and let.... Uhhh... Meee... Unnngggg... In!"

"Ahhhgg Ohhh Lord! Oh Lord Sterling... N-noooo! Uhhhh Oh you're... You're ki-kill - killlling - meeee!" I cried as he pushed, holding me at my hips and drawing me back but by now I was powerless against him... I couldn't stop him or hold him back any longer...

"Uhhhh! Yes! Fuck yes... Take that cock my little fag-boy... Take me dry.... Uhhh yes... Feel that? Feel me going in? Every -Uhhhh- Last -Uhhh- Inch!"

Howling as he pushed on I could hardly stand the pain as everything turned white, it felt like his cock was made of molten steel as my body and ass resisted but still he forced his way in, and as he said, making me feel every last inch. I couldn't help but to go rigid and clench up, letting him in like this, my body was doing everything it could to not let it happen...

Like a self-preservation law stepping in, the kind that stops you from flinging yourself off a 20-story balcony, with a will of it's own my body was trying to stop him, but Lord Sterling, wanting to cause me pain as he fucked me bare-back and bone-dry, to have me suffer for him, he pressed on. Uncaring and without relent he fed me each agonizing, slow, flesh-tearing inch of that 9-inch steely-snake he calls a cock... That Lock-Ness-Monster my English Master keeps in his loose, Egyptian cottons...

"Uhhhh! Ohhh plee-eese!" I cried again as he continued until I felt him there, the back's of his thighs touching mine, his weight bearing down on top of me, crouching and talking into my ear...

"That's it boy... Take me... Feel me Dana, feel my big old cock all the way up inside of you... I know it may hurt but you took me well and without any aid... Do you know what that tells me?" Lord Sterling asked as I struggled beneath him thinking and believing that I'd never adjust as I took his bait, asking, wanting to know what he knows. What my gay Lord and Master knows about me...

"N-no?" I gasped... "Wh-what does it tell you?" I grunted asking in a fought for breath, yet of my question, I didn't want to hear his answer...

"Uhhh" Lord Sterling grunted then, grinding into me, buried deep and keeping himself there as I did the same... Groaning but for a very different reason I moaned back feeling his every movement, his thick, hard cock felt like it was covered in glass, the stinging prickling pain of being impaled dry as I was, it didn't fade or go away but instead, it only grew worse...

"What it tells me Dana is that you are a true gay-boy, a real man's fag who will take any cock anytime or anywhere... This is why you were put on this Earth... To serve men, to serve cock... And that includes using lubrication... Or not! Unnnnggg! Uhhh! Yesss... Take it... Take my cock, be my fag and say it Dana... Tell me who you.... Uhhhh... Are.... Uhhh"

"Ohhh God! Oh fuu-uuck that... Of fuck meeee that huuuu-uuuurts!" I wailed as Lord Sterling not only spoke to me in such rude, crude terms, but to prove his point and literally drive it home he began to fuck me as I was... As he was saying... I was taking him and his cock at any measure...and I felt it as well... Being dry-fucked... I felt like not just his 'gay-boy' but rather I was his 'man's-fag' someone men can fuck and abuse at will and to their liking...

"You would do well in prison Dana but thankfully I found you first... Uhh... Uhh... Unngg... Oh fuck that is good... What a way to wake up in the morning... Oh and this is something else I'm coming to love about you... You make me cum like no other boy I've had... Oh yes! It's me who should be thankful... Uhhh! Uhhh Oh yes I'm going to.... Oh! Yes here... Take... Take meeee... Unnnnggg"...

Racked in so much pain it was to the point where I couldn't talk and was hardly able to keep the air in my lungs, all I could do was stay there in the bed and take it... Take what Lord Sterling was giving me... Fucking me in and out with his hard, unwavering 9-inches.

Cumming then deep inside me I could feel him pulse, his cock throbbing as his low hanging balls pumped and contracted, dumping this early morning load of cum into my otherwise accepting body...

"Uhhh Ohh... Oh my Lord please g-go slow c-coming back ouu-uut! Ohhh!" I groaned in another pained sigh feeling the big man's still hard yet spent cock making it's retreat. Every excruciating inch pulling and scrapping its way back out of my rear passage was pure agony... Each gut wrenching ripple, vein and nuance, I held my breath expecting and feeling so much pain...

Not even his cum being used as the missing lube could help me now as it came spilling out after him, exiting with his cock, left running out of me and down the inner backs of my thighs as I stayed up-right, my ass presented and my face still buried into the pillows.

I could feel the wetness as well as the vacancy, being empty and no longer stuffed with cock, it was a weird eerie feeling I wasn't sure if I would ever get used to...

It was something I couldn't understand that I first noticed when Veronica had used our dildo on me back home, fucking my ass with the life-like sex toy aptly named 'little-Reg' until she had me cumming hard and begging for more... But then after, once it was finished and she had pulled the long, thick rubbery dildo from my ass, I had this feeling come over me, this longing, this wanting of wishing it was still there... Wishing I was still full of cock...

But why? Why did I miss it so? The thing that was humiliating me, fucking me and taking away my manhood with a mix of pain filled pleasure... I couldn't see and I didn't know why...

Why like a warm blanket being torn away... Why did I miss it so dearly and where more than anything else, I wanted it back?

It was a mystery like all other I suppose... Like Deja-vu... I mean... Where the hell does that anomaly in our brains come from?

***

Falling and collapsing down onto the bed-sheets I felt Lord Sterling leaving, climbing off the bed and disappearing into the en-suite, no doubt to empty his pent-up and held bladder. Having his morning piss and revealing the pressure that had made him so hard in the first place.

Hard enough to not just fuck me but literally he was 'tearing me a new one' by fucking me dry...

Laying there and doing my own form of recovery I began to think and remember, I felt a different kind of emptiness creeping in as I realized that it had been nearly a week now since Veronica and Brother Reg had taken the water taxi over to a different island. One where Brother Reg said he had a distant cousin he wanted to visit and was to put them up in a cabin, just so they could be truly alone...

Which I found kind of strange and unsettling as they told, leaving me to think they already had a place to themselves right here and now that I was out of their hair and staying Lord Sterling, they would have all of the alone-time they would need... Alone to fuck and make a baby... 'Our' child that they were trying to conceive...

I did feel sad for a moment, but more so I was reminiscing and thinking of the past but included in there was my Mom, who as it turns out? She was the silver lining in all of this... She would be the end to my loneliness because as of later that after noon, she would be here, joining us after flying down to start her leg of this winter's long vacation in the Sun that we had all embarked upon...

***

Learning as I went in the earliest days and as we began to develop a pattern, I was discovering that not only was I living as Lord Sterling's gay partner, as his 'bottom', or to be blunt, his personal cum dump, or even 'fuck-toy'... But as well, and aside from the times he was balls deep in my throat or my ass -with lube up until now, and along with all of the gay sex, I was also acting as his servant, his care-taker and personal go-boy, or 'dog's-body' as he called me using his English words and phrases.

Which meant as I heard the toilet flush and then his morning shower being turned on I knew enough that my next job was to get up and strip the bed, pulling off the cum-wet bed sheets in a bundle and take them out to the laundry bins where they would be picked up by the other service he uses... The laundry service...

Moving slower than usual and needing the bathroom myself I hurried along as fast as I could, sighing and wincing with my poor battered ass still reeling from the effects of Lord Sterling's giving me this introduction to the horrors of dry fucking, or anal-rape, what it felt like...

Like he was indeed 'prison-fucking' me as he had eluded, saying that I would do well behind bars, but as my ass stung I chose not to focus on that certain nightmare scenario.. So instead and on a happier note I smiled thinking that in a few short hours Mom would be here and I wouldn't be so alone anymore...

We hadn't talked much in the days and weeks leading up to today, her arrival date... So aside from being excited about her coming, I was also feeling somewhat apprehensive wondering how she would react to these changes I had been making, or going through and with her it was namely my clothing that I was worried about...

Mom was quite keen on my feminization even going so far as to pay for my hormone treatments and with the clothing, or my cross dressing to the point where all I was wearing were either the old clothes belonging to Veronica or the new things Mom kept coming over with, and if you'll remember she was the one who had me out in public wearing a dress for the first time.

So yeah, with how Lord Sterling had said that although he wanted to keep me on the hormones because he liked how soft and 'feminine-like' they kept me, and how my titties were developing, he thought that part was cute... But as for my female clothing, as he had also stated, he wanted a gay-male partner and not a lady-boy like they have in Asia and the Philippines where the gay-boys do all they can to look and act like girls and women.... And damn are they ever convincing!

And as far as he was concerned with my little dick? As of this time he was still insisting that I stay locked up and kept in chastity, saying how he liked thinking of me as being without genitals but I wasn't sure I understood him so of course I didn't dare say anything.

Along with this, it wasn't an issue for him when I told him that I wasn't getting hard anymore and rarely did I feel uncomfortable in my cage as I once did at times when I was most aroused. I noticed it first in the morning where unlike my Master and Lord, he was steely-hard and huge when rising and even for a man of his age, it didn't seem to matter... Yet here I was, taking female-replacement hormones and at half his age, and with my little dick? I could hardly feel a thing...

In fact, and along the same lines of liking the idea of me not having dick he told me a story about an island not far from where were, an island of Eunuch's or 'boys like me' as he added, sounding casual as he went on telling me how these men were put there as punishment for crimes and treated as castaways.

As frightening as this sounded all by itself, but according to Lord Sterling and even scarier still was that all of the prisoners upon their arrival, they are force-castrated, having their balls cut off for real.

Meant to scare me I'm sure but with how he said it, and in comparison to my no longer feeling much or any arousal through my caged dick? I wasn't so sure what he was trying to tell me, but being far too scary a thing to imagine, I tried to forget it and put it out of my mind... Yet warily I was always on my toes and behaving myself how he wanted.

Choosing what to wear for my Mom's arrival, that's what I should have been thinking of, and although still worried about how she was going to see me, looking not-so-girly dressed in one of my most decidedly gay-sailor suits. The ones made from silk and consisting of nothing more than a pair of short-shorts that were indeed so short and tight they split my ass cheeks, riding up my back side and holding me tight with little to no give at all.

Sighing, I knew this would be just another one of those bridges I would have to cross when I came to it, and besides, other than showing up naked, which I had been quite often as we lounged around in the Sun, but with Lord Sterling having taken away all of the clothes I had with me and where instead I had been given this wardrobe consisting of silk robes, half-tops and tight little pairs of shorts, all in matching colours of course, to make me look like I was in a uniform of sorts...

Or my gay-boy uniform is what I called my new clothes, and to be honest? Sometimes I preferred being naked, I found it much more freeing and comfortable...

Even if that did include being seen by the staff, but they never said anything to me, just smiling seeing me in my pink little chastity cage and nothing else as they brought me drinks and my lunch.

Nervous with the hour drawing near it wasn't long before Lord Sterling appeared from somewhere in the big house...

"Ah there you are Dana-boy... It's almost time I see, Philippe the taxi driver will have your Mother here soon, are you ready to meet her? I know I'm intrigued... I'm sure she's quite lovely and I know she'll be a wealth of knowledge, telling me all I will need to know about you... Hmm?"

"Yes... She's not afraid to tell people all about me, but I am a little worried because she might not like the new changes I've been going through... With you I mean" I replied but Lord Sterling he looked at me a little concerned, not understanding...

"What are you saying Dana-boy? Will she be unhappy with you coming out and admitting who you are? Telling us all that you're gay and that you want to be with me as my consort, my gay-boy in training, let's say?"

"N-no... It's not that... It's about my clothes and how she wanted me to be like the daughter she never had... I just don't want her to be disappointed now that you have me dressing and acting d-differently" I replied with a stutter at the end hoping my bringing this up didn't upset him...

"Oh I wouldn't be too worried about that my boy... If I know anything about Mother's it's that they love their children without condition, and with her already accepting you wanting to dress and act like a girl, which may be fun for you but it is a cover, a way of denying who you really are... A gay man, as you've admitted to us all.... But otherwise I can't see her taking much issue" Lord Sterling replied as he walked me to the waiting car that would take us down to the long pier-like dock where the boats come in from the mainland.

Listening to him however, I did feel myself sink a little knowing now that I was going to have to come out once again but this time to my Mom and as accepting as I knew she was going to be, or unconditional as Lord Sterling was saying... But still, I did feel the butterflies coming back, filling my stomach and making me nervous...

Excited to see my Mom after this near month long absence I was also apprehensive and afraid. But that was just me... As always...

***

Down at the docks...

"Hi there! Hello! I made it! I can't believe I'm here!" Mom called out as Lord Sterling and I stood on the rickety old wooden pier watching as the long, thin and rather fast moving boat came in, close enough now and with it's motor turned off we could hear her calling out and waving from her back-wards facing seat, the smile and joy on her face, I didn't remember ever seeing her looking so happy...

"Hi Mom! I said back to her, smiling and waving genuinely pleased to see her as the boat pulled in with me reaching out to take her hand as Lord Sterling in a rare showing he helped Philippe tie off the ropes.

Standing and wobbling some, I was afraid she was going to fall over board but Philippe was there in a second to catch her from behind as she turned looking and smiling to him while thanking him as they shared what looked like a knowing glance, and catching my eye I found it rather peculiar...

"Thank you Philippe, you've been very kind and I'm sorry again but I didn't have any pesos to tip you with... I hope I was able to ummm, take care of you when we stopped out on the water?" She asked with her voice sounding smooth and intoxicated, she sounded half drunk if I didn't know any better.